Trifluoroacetic acid → HCID 178489469, compound

HRID 539105Notes

Reaction equation

HRID 539105 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][C:27]([N:30]4[C@@H:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[O:41][CH3:42])[CH2:33][O:32][C:31]4=[O:43])=[N:26][C:25]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][N:10](COCC[Si](C)(C)C)[N:9]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][C:27]([N:30]4[C@@H:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[O:41][CH3:42])[CH2:33][O:32][C:31]4=[O:43])=[N:26][C:25]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][NH:10][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68088961(S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-methoxyphenyl) oxazolidin-2-one

Product 1

HCID 178489469HCID 178489469, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-methoxyphenyl) oxazolidin-2-one (0.0424 g, 0.071 mmol) in DCM (1 mL) was treated with trifluoroacetic acid (0.5 mL) at ambient temperature. The mixture was stirred for 18 hours. The solvent was concentrated and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was further extracted with EtOAc and DCM. The combined organic extracts were washed with brine, dried, and concentrated, and the crude material was purified by column chromatography (silica, 10% MeOH/dichloromethane) to afford the title compound (0.011 g, 33%) as a yellow solid. MS (APCI+) m/z 472 [M+H]+.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. extractionThe aqueous layer was further extracted with EtOAc and DCM
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customthe crude material was purified by column chromatography (silica, 10% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-991e2d2d172849ca86a2d5f222b47e2d
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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